CA1224419A - Pharmaceutical and veterinary compositions for the treatment of ischemic cardiac disorders - Google Patents

Pharmaceutical and veterinary compositions for the treatment of ischemic cardiac disorders

Info

Publication number: CA1224419A
Authority: CA; Canada
Prior art keywords: composition; composition according; dosage unit; unit form; benzofuran
Prior art date: 1983-08-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000459483A

Other languages

English (en)

French (fr)

Inventor

Marcel Descamps

Yves Berger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi SA

Original Assignee

Sanofi SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-08-02

Filing date

1984-07-23

Publication date

1987-07-21

1984-07-23 Application filed by Sanofi SA filed Critical Sanofi SA

1987-07-21 Application granted granted Critical

1987-07-21 Publication of CA1224419A publication Critical patent/CA1224419A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 56
238000011282 treatment Methods 0.000 title abstract description 6
208000020446 Cardiac disease Diseases 0.000 title abstract description 4
208000019622 heart disease Diseases 0.000 title abstract description 4
230000000302 ischemic effect Effects 0.000 title abstract description 4
239000002253 acid Substances 0.000 claims abstract description 19
150000001907 coumarones Chemical class 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 12
-1 monoethylamino Chemical group 0.000 claims abstract description 8
MDUQQNWSTJAPCW-UHFFFAOYSA-N (ethyl-$l^{2}-azanyl)ethane Chemical compound CC[N]CC MDUQQNWSTJAPCW-UHFFFAOYSA-N 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 27
238000007911 parenteral administration Methods 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
HEPAWQLOFNBDPR-UHFFFAOYSA-N (2-butyl-1-benzofuran-3-yl)-[4-[2-(ethylamino)ethoxy]phenyl]methanone Chemical group CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(OCCNCC)C=C1 HEPAWQLOFNBDPR-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
VXOKDLACQICQFA-UHFFFAOYSA-N N-Desethylamiodarone Chemical group CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCNCC)C(I)=C1 VXOKDLACQICQFA-UHFFFAOYSA-N 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 3
239000004480 active ingredient Substances 0.000 abstract description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 abstract description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
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DKWLFFXBYKTKRM-UHFFFAOYSA-N (2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3-iodophenyl]methanone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(OCCN(CC)CC)C(I)=C1 DKWLFFXBYKTKRM-UHFFFAOYSA-N 0.000 description 2
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239000013078 crystal Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940041476 lactose 100 mg Drugs 0.000 description 1
210000005246 left atrium Anatomy 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
230000004118 muscle contraction Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
229960003343 ouabain Drugs 0.000 description 1
230000036284 oxygen consumption Effects 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229960001462 sodium cyclamate Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000036977 tonic contraction Effects 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002966 varnish Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
General Health & Medical Sciences (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)

CA000459483A 1983-08-02 1984-07-23 Pharmaceutical and veterinary compositions for the treatment of ischemic cardiac disorders Expired CA1224419A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8312739A FR2550091B1 (fr)	1983-08-02	1983-08-02	Composition pharmaceutique ou veterinaire destinee a combattre des troubles ischemiques cardiaques contenant un derive du benzofuranne
FR8312739		1983-08-02

Publications (1)

Publication Number	Publication Date
CA1224419A true CA1224419A (en)	1987-07-21

Family

ID=9291337

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000459483A Expired CA1224419A (en)	1983-08-02	1984-07-23	Pharmaceutical and veterinary compositions for the treatment of ischemic cardiac disorders

Country Status (12)

Country	Link
US (3)	US4575513A (da)
EP (1)	EP0133176B1 (da)
JP (1)	JPS6054316A (da)
AU (1)	AU568135B2 (da)
BE (1)	BE900138A (da)
CA (1)	CA1224419A (da)
DE (1)	DE3460620D1 (da)
DK (1)	DK162736C (da)
FR (1)	FR2550091B1 (da)
IL (1)	IL72425A (da)
NZ (1)	NZ209072A (da)
ZA (1)	ZA845271B (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1990007329A1 (en) *	1989-01-06	1990-07-12	The Regents Of The University Of California	Selection method for pharmacologically active compounds
US5234949A (en) *	1992-04-01	1993-08-10	Academic Pharmaceuticals, Inc.	Parenteral solutions containing amiodarone in acetate buffer solution
FR2746013B1 (fr) *	1996-03-18	1998-05-29	Sanofi Sa	Utilisation de composes antiarythmiques dans la prevention de la mortalite post infarctus
US6030998A (en) *	1997-06-27	2000-02-29	Academic Pharmaceuticals, Lp	Methods for treating arrhythmia using acetate buffer solutions of amiodarone
RU2212236C1 (ru) *	2002-09-05	2003-09-20	Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин"	Антиаритмическая, антиангинальная фармацевтическая композиция
WO2005099684A1 (en) *	2004-04-09	2005-10-27	Aryx Therapeutics	Benzofuranyl derivatives useful for the treatment of cardiac arrhythmia
EP1904502B1 (en) *	2005-07-15	2009-10-21	Aryx Therapeutics, Inc.	Antiarrhythmic precursor compounds, methods of synthesis and methods of use
WO2013158251A1 (en) *	2012-04-17	2013-10-24	Scifluor Life Sciences, Llc	Fluorinated benzofuran derivatives
EP2674158B9 (en) *	2012-06-14	2015-11-18	Szegedi Tudományegyetem	Treatment and prevention of cardiac arrhythmias
CN114671836B (zh) *	2021-12-30	2025-04-18	南京望知星医药科技有限公司	一种胺碘酮杂质c的合成方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4024273A (en) *	1974-06-20	1977-05-17	Smithkline Corporation	Coronary vasodilator and anti-anginal compositions comprising substituted benzofurans and benzothiophenes and methods of producing coronary vasodilation and anti-anginal activity
IT1154888B (it) *	1980-11-12	1987-01-21	Menarini Sas	Derivati del benzofurano 2-sostituiti e relativi metodi di preparazione
FR2549475B1 (fr) *	1983-07-18	1986-02-07	Labaz Sanofi Nv	Nouveaux derives de benzofuranne, leur preparation et leur utilisation therapeutique

1983
- 1983-08-02 FR FR8312739A patent/FR2550091B1/fr not_active Expired
1984
- 1984-07-05 US US06/628,210 patent/US4575513A/en not_active Expired - Fee Related
- 1984-07-09 ZA ZA845271A patent/ZA845271B/xx unknown
- 1984-07-12 EP EP84870101A patent/EP0133176B1/fr not_active Expired
- 1984-07-12 BE BE0/213317A patent/BE900138A/fr not_active IP Right Cessation
- 1984-07-12 DE DE8484870101T patent/DE3460620D1/de not_active Expired
- 1984-07-17 IL IL72425A patent/IL72425A/xx unknown
- 1984-07-19 AU AU30832/84A patent/AU568135B2/en not_active Ceased
- 1984-07-23 CA CA000459483A patent/CA1224419A/en not_active Expired
- 1984-07-23 DK DK360884A patent/DK162736C/da not_active IP Right Cessation
- 1984-07-31 JP JP59162762A patent/JPS6054316A/ja active Pending
- 1984-08-01 NZ NZ209072A patent/NZ209072A/en unknown
1985
- 1985-12-11 US US06/807,733 patent/US4661514A/en not_active Expired - Fee Related
1986
- 1986-12-02 US US06/936,776 patent/US4791137A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU3083284A (en)	1985-02-07
DK360884D0 (da)	1984-07-23
IL72425A (en)	1987-12-31
FR2550091A1 (fr)	1985-02-08
EP0133176B1 (fr)	1986-09-03
DK162736C (da)	1992-04-27
US4791137A (en)	1988-12-13
US4575513A (en)	1986-03-11
EP0133176A1 (fr)	1985-02-13
DE3460620D1 (en)	1986-10-09
BE900138A (fr)	1985-01-14
NZ209072A (en)	1987-01-23
IL72425A0 (en)	1984-11-30
FR2550091B1 (fr)	1986-05-23
AU568135B2 (en)	1987-12-17
US4661514A (en)	1987-04-28
JPS6054316A (ja)	1985-03-28
ZA845271B (en)	1985-02-27
DK360884A (da)	1985-02-03
DK162736B (da)	1991-12-09

Legal Events

Date	Code	Title	Description
2004-07-23	MKEX	Expiry

Publication	Publication Date	Title
US4228187A (en)	1980-10-14	Alkyl and cycloalkylthiophenylalkylaminoalkanols, their salts and the preparation thereof
CA1224419A (en)	1987-07-21	Pharmaceutical and veterinary compositions for the treatment of ischemic cardiac disorders
US3793365A (en)	1974-02-19	Amino acid derivatives
EP0345592B1 (en)	1993-08-11	Novel 2-substituted coumaran derivatives
US4659710A (en)	1987-04-21	1,7-Naphthyridine derivatives and pharmaceutical compositions
NO156525B (no)	1987-06-29	Analogifremgangsmaate ved fremstilling av terapeutisk aktive (3-aminopropoksy)bibenzylderivater.
NO167658B (no)	1991-08-19	Analogifremgangsmaate for fremstilling av nye, terapeutiskaktive difenylpropylaminderivater.
AU618595B2 (en)	1992-01-02	Derivative of caffeic acid and pharmaceutical composition containing the same
JPS59161392A (ja)	1984-09-12	ジヒドロピリジン誘導体及びその製法
JPH03287586A (ja)	1991-12-18	テトラヒドロ―β―カルボリン誘導体
DE3248957C2 (da)	1989-09-21
EP0816338B1 (en)	2003-02-12	3-(bis-substituted-phenylmethylene)oxindole derivatives
EP0089634B1 (en)	1986-07-02	Phenoxypropanolamine derivatives
US4187313A (en)	1980-02-05	2-Aminoethyl-1,4-benzodioxans
US3562297A (en)	1971-02-09	Alkanolamine derivatives
CA1228862A (en)	1987-11-03	Azulene derivatives, processes of their synthesis and their uses as anti-ulcerative and anti-inflammatory agents
EP0300725A1 (en)	1989-01-25	Tetrahydroisoquinolin-2-yl derivatives as thromboxane A2 antagonists
US4742062A (en)	1988-05-03	Benzylpiperazine compound and pharmaceutical composition as hypolipidemic agent
US4565828A (en)	1986-01-21	Benzofuran derivatives and their therapeutic use
US4517365A (en)	1985-05-14	Isocarbostyril derivative
US4140790A (en)	1979-02-20	3-(4-Substituted piperazino)-1-xanthene-9-carbonyloxy-propanes
US4199582A (en)	1980-04-22	Piperazine containing dihydronaphthalene derivatives and compositions
US5059607A (en)	1991-10-22	Imidazolyl benzisoquinolines useful as 5-ht3 receptor antagonists
US4378362A (en)	1983-03-29	Indolizine derivatives and process for preparing the same
US3985896A (en)	1976-10-12	Benzophenalenofurans